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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1165.
Published online 2009 April 30. doi:  10.1107/S1600536809015232
PMCID: PMC2977830

2-(3-Methoxy­phen­yl)butane­dinitrile

Abstract

In the title compound, C11H10N2O, the dicyano­ethyl­ene portion has an anti conformation. The crystal structure features non-classical C—H(...)N and C—H(...)O inter­actions.

Related literature

For the synthesis, see: Johnson et al. (1962 [triangle]). The title compound is an inter­mediate in the synthesis of drugs (Obniska et al., 2005 [triangle]).

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Object name is e-65-o1165-scheme1.jpg

Experimental

Crystal data

  • C11H10N2O
  • M r = 186.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1165-efi1.jpg
  • a = 5.5263 (8) Å
  • b = 16.105 (2) Å
  • c = 11.0332 (16) Å
  • β = 97.179 (2)°
  • V = 974.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.4 × 0.2 × 0.1 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: none
  • 8042 measured reflections
  • 2210 independent reflections
  • 1963 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.128
  • S = 1.04
  • 2210 reflections
  • 128 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015232/ng2569sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015232/ng2569Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Science and Technology Fund of Anhui Province for Outstanding Youth (No. 08040106906), the National Natural Science Foundation (No. 20671002) of China, the State Education Ministry (EYTP, SRF for ROCS, SRFDP 20070370001) and the Education Department (No. 2006KJ006TD) of Anhui Province.

supplementary crystallographic information

Comment

The title compound is an important intermediate in drugs synthesis (Obniska et al., 2005). In this paper, we report the structure of the title compound (I). In (I), the succinonitrite moiety adopts an anti conformation. Six atoms of succinonitrite moiety, (N1/C9/C8/N2/C11/C10), almost lie on one plane, the maximum deviations from the mean plane of the succinonitrite being 0.0275 (8) Å. This mean plane is almost perpendicular to the phenyl mean plane with a dihedral angle of 87.55 (6) Å. The crystal packing is stabilized by two intermolecular non-classic C—H···N hydrogen bonds and one intermolecular non-classic C—H···O hydrogen bond.

Experimental

The compound (I) was obtained by reaction of (Z)-ethyl-2-cyano-3-(4-methoxyphenyl)acrylate and NaCN in ethanol-water mixture according to the reported method (Johnson et al., 1962). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.

Refinement

All non-hydrogen atoms were refined anisotropically. H atoms bonded to C atoms were introduced at calculated positions and refined using a riding model with C—H distances of 0.93–0.97 Å. In all cases, the H-atom Uiso(H) is 1.2 times Ueq of the parent atom.

Figures

Fig. 1.
The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A packing diagram of (I) viewed down the a axis. Dotted lines show the C—H···N and C—H···O hydrogen bonds.

Crystal data

C11H10N2OF(000) = 392
Mr = 186.21Dx = 1.270 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5752 reflections
a = 5.5263 (8) Åθ = 2.3–27.4°
b = 16.105 (2) ŵ = 0.08 mm1
c = 11.0332 (16) ÅT = 298 K
β = 97.179 (2)°Block, colorless
V = 974.3 (2) Å30.4 × 0.2 × 0.1 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer1963 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
graphiteθmax = 27.5°, θmin = 2.3°
[var phi] and ω scansh = −7→7
8042 measured reflectionsk = −20→20
2210 independent reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0729P)2 + 0.1612P] where P = (Fo2 + 2Fc2)/3
2210 reflections(Δ/σ)max = 0.001
128 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.21 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C60.6739 (2)0.85144 (7)0.67253 (10)0.0379 (3)
C70.5211 (2)0.80066 (7)0.73097 (11)0.0406 (3)
H70.41770.82370.78220.049*
C50.8292 (3)0.81733 (9)0.59747 (12)0.0518 (3)
H50.93210.85120.55880.062*
C20.5237 (2)0.71565 (7)0.71258 (11)0.0439 (3)
C30.6789 (3)0.68150 (8)0.63618 (14)0.0551 (4)
H30.67990.62450.62310.066*
C40.8306 (3)0.73211 (9)0.58018 (15)0.0622 (4)
H40.93580.70900.52990.075*
C80.6709 (2)0.94492 (7)0.69077 (10)0.0384 (3)
H80.78910.96980.64230.046*
C100.7385 (2)0.97151 (7)0.82538 (11)0.0414 (3)
H10A0.73111.03150.83110.050*
H10B0.62090.94850.87440.050*
C90.4279 (2)0.97888 (7)0.64751 (11)0.0435 (3)
O10.37911 (19)0.66090 (5)0.76429 (10)0.0605 (3)
C10.2421 (3)0.69035 (10)0.85616 (15)0.0638 (4)
H1A0.35050.71410.92180.096*
H1B0.15450.64500.88670.096*
H1C0.12860.73180.82210.096*
N10.2393 (2)1.00418 (8)0.61421 (12)0.0604 (3)
C110.9826 (2)0.94328 (7)0.87350 (10)0.0415 (3)
N21.1722 (2)0.92210 (8)0.91331 (11)0.0581 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C60.0380 (6)0.0381 (6)0.0376 (5)−0.0021 (4)0.0054 (4)−0.0030 (4)
C70.0415 (6)0.0363 (6)0.0462 (6)−0.0003 (4)0.0139 (5)−0.0042 (4)
C50.0540 (8)0.0522 (7)0.0537 (7)−0.0070 (6)0.0239 (6)−0.0074 (5)
C20.0443 (6)0.0368 (6)0.0518 (6)−0.0028 (5)0.0112 (5)−0.0029 (5)
C30.0617 (8)0.0384 (6)0.0679 (8)0.0001 (5)0.0188 (6)−0.0143 (6)
C40.0668 (9)0.0565 (8)0.0696 (9)−0.0002 (7)0.0339 (7)−0.0175 (7)
C80.0364 (6)0.0373 (6)0.0417 (6)−0.0028 (4)0.0053 (4)0.0024 (4)
C100.0399 (6)0.0366 (5)0.0467 (6)0.0036 (4)0.0019 (5)−0.0048 (4)
C90.0436 (7)0.0397 (6)0.0460 (6)−0.0049 (5)0.0007 (5)0.0055 (5)
O10.0694 (7)0.0352 (5)0.0829 (7)−0.0077 (4)0.0339 (5)−0.0025 (4)
C10.0727 (10)0.0539 (8)0.0708 (9)−0.0093 (7)0.0331 (8)0.0033 (7)
N10.0479 (7)0.0619 (7)0.0679 (8)0.0001 (5)−0.0065 (5)0.0126 (6)
C110.0429 (6)0.0402 (6)0.0413 (6)0.0009 (5)0.0050 (5)−0.0025 (4)
N20.0469 (6)0.0739 (8)0.0525 (6)0.0129 (5)0.0023 (5)−0.0037 (5)

Geometric parameters (Å, °)

C6—C51.3791 (16)C8—C91.4730 (16)
C6—C71.3903 (15)C8—C101.5460 (16)
C6—C81.5193 (15)C8—H80.9800
C7—C21.3843 (16)C10—C111.4593 (16)
C7—H70.9300C10—H10A0.9700
C5—C41.386 (2)C10—H10B0.9700
C5—H50.9300C9—N11.1365 (16)
C2—O11.3623 (15)O1—C11.4205 (17)
C2—C31.3890 (17)C1—H1A0.9600
C3—C41.371 (2)C1—H1B0.9600
C3—H30.9300C1—H1C0.9600
C4—H40.9300C11—N21.1368 (16)
C5—C6—C7120.25 (11)C6—C8—C10113.36 (9)
C5—C6—C8119.48 (10)C9—C8—H8108.3
C7—C6—C8120.28 (9)C6—C8—H8108.3
C2—C7—C6119.71 (10)C10—C8—H8108.3
C2—C7—H7120.1C11—C10—C8111.38 (9)
C6—C7—H7120.1C11—C10—H10A109.4
C6—C5—C4119.46 (12)C8—C10—H10A109.4
C6—C5—H5120.3C11—C10—H10B109.4
C4—C5—H5120.3C8—C10—H10B109.4
O1—C2—C7124.16 (11)H10A—C10—H10B108.0
O1—C2—C3115.90 (11)N1—C9—C8179.20 (13)
C7—C2—C3119.94 (11)C2—O1—C1118.40 (10)
C4—C3—C2119.79 (11)O1—C1—H1A109.5
C4—C3—H3120.1O1—C1—H1B109.5
C2—C3—H3120.1H1A—C1—H1B109.5
C3—C4—C5120.84 (12)O1—C1—H1C109.5
C3—C4—H4119.6H1A—C1—H1C109.5
C5—C4—H4119.6H1B—C1—H1C109.5
C9—C8—C6110.45 (9)N2—C11—C10178.53 (13)
C9—C8—C10108.02 (9)
C5—C6—C7—C2−0.64 (18)C6—C5—C4—C30.3 (2)
C8—C6—C7—C2179.32 (11)C5—C6—C8—C9118.72 (12)
C7—C6—C5—C40.4 (2)C7—C6—C8—C9−61.25 (14)
C8—C6—C5—C4−179.55 (13)C5—C6—C8—C10−119.90 (12)
C6—C7—C2—O1−179.11 (11)C7—C6—C8—C1060.14 (14)
C6—C7—C2—C30.13 (19)C9—C8—C10—C11−177.45 (10)
O1—C2—C3—C4179.91 (14)C6—C8—C10—C1159.81 (13)
C7—C2—C3—C40.6 (2)C7—C2—O1—C1−9.4 (2)
C2—C3—C4—C5−0.8 (2)C3—C2—O1—C1171.30 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8···N1i0.982.613.4864 (17)150
C10—H10A···O1ii0.972.383.2470 (15)149
C10—H10B···N2iii0.972.603.4823 (18)151

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2569).

References

  • Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Johnson, F., Panella, J. P. & Carlson, A. A. (1962). J. Org. Chem.28, 2241–2243.
  • Obniska, J., Jurczyk, S., Zejc, A., Kamiński, K., Tatarczyńska, E. & Stachowicz, K. (2005). Pharmacol. Rep.57, 170–175. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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